CA1230697A - Epoxy-urethane avec liaison alcanolamine - Google Patents

Epoxy-urethane avec liaison alcanolamine

Info

Publication number: CA1230697A
Authority: CA; Canada
Prior art keywords: epoxy; ethanolamine; urethane; equivalents; vibrathane
Prior art date: 1984-08-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000478524A

Other languages

English (en)

Inventor

Douglas J. Tosh

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mapei Inc

Original Assignee

Sternson Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-08-31

Filing date

1985-04-04

Publication date

1987-12-22

1985-04-04 Application filed by Sternson Ltd filed Critical Sternson Ltd

1987-12-22 Application granted granted Critical

1987-12-22 Publication of CA1230697A publication Critical patent/CA1230697A/fr

Status Expired legal-status Critical Current

Links

JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 40
239000000203 mixture Substances 0.000 claims abstract description 34
239000004593 Epoxy Substances 0.000 claims abstract description 31
-1 N-substituted ethanolamine Chemical class 0.000 claims abstract description 14
239000003795 chemical substances by application Substances 0.000 claims abstract description 14
239000004850 liquid epoxy resins (LERs) Substances 0.000 claims abstract 8
KYUPIHBUKDNZKE-UHFFFAOYSA-N 1-amino-3-methylbutan-2-ol Chemical compound CC(C)C(O)CN KYUPIHBUKDNZKE-UHFFFAOYSA-N 0.000 claims abstract 7
LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical group CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims abstract 4
229920000647 polyepoxide Polymers 0.000 claims description 24
239000003822 epoxy resin Substances 0.000 claims description 21
239000012948 isocyanate Substances 0.000 claims description 18
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 17
150000002513 isocyanates Chemical class 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 16
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 11
239000007795 chemical reaction product Substances 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000007788 liquid Substances 0.000 claims description 9
239000004014 plasticizer Substances 0.000 claims description 9
229920001730 Moisture cure polyurethane Polymers 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
125000003700 epoxy group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
239000000945 filler Substances 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 2
229920000728 polyester Polymers 0.000 claims description 2
229920000570 polyether Polymers 0.000 claims description 2
150000002924 oxiranes Chemical class 0.000 claims 12
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 claims 3
238000012544 monitoring process Methods 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 44
229920005989 resin Polymers 0.000 abstract description 29
239000011347 resin Substances 0.000 abstract description 29
229920002803 thermoplastic polyurethane Polymers 0.000 abstract description 16
239000012528 membrane Substances 0.000 abstract description 7
239000000853 adhesive Substances 0.000 abstract description 6
230000001070 adhesive effect Effects 0.000 abstract description 6
239000000565 sealant Substances 0.000 abstract description 6
238000004078 waterproofing Methods 0.000 abstract description 5
150000002118 epoxides Chemical class 0.000 description 17
239000000047 product Substances 0.000 description 14
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
229940031098 ethanolamine Drugs 0.000 description 4
238000009472 formulation Methods 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
235000018936 Vitellaria paradoxa Nutrition 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000008859 change Effects 0.000 description 3
238000013329 compounding Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
150000003673 urethanes Chemical class 0.000 description 3
229920003319 Araldite® Polymers 0.000 description 2
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000002184 metal Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000011342 resin composition Substances 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 description 1
ZKKBPHUAHARETG-UHFFFAOYSA-N 4-methylhexan-2-amine;hydrochloride Chemical compound Cl.CCC(C)CC(C)N ZKKBPHUAHARETG-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
235000009434 Actinidia chinensis Nutrition 0.000 description 1
244000298697 Actinidia deliciosa Species 0.000 description 1
235000009436 Actinidia deliciosa Nutrition 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
241000490229 Eucephalus Species 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000201776 Steno Species 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
ZHNUHDYFZUAESO-OUBTZVSYSA-N aminoformaldehyde Chemical compound N[13CH]=O ZHNUHDYFZUAESO-OUBTZVSYSA-N 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
239000004567 concrete Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
235000021438 curry Nutrition 0.000 description 1
238000007872 degassing Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003607 modifier Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000013031 physical testing Methods 0.000 description 1
239000010665 pine oil Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000037452 priming Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000010512 small scale reaction Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Polyurethanes Or Polyureas (AREA)

CA000478524A 1984-08-31 1985-04-04 Epoxy-urethane avec liaison alcanolamine Expired CA1230697A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US646,702		1984-08-31
US06/646,702 US4520185A (en)	1984-08-31	1984-08-31	Alkanolamine linked epoxy-urethanes

Publications (1)

Publication Number	Publication Date
CA1230697A true CA1230697A (fr)	1987-12-22

Family

ID=24594123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000478524A Expired CA1230697A (fr)	1984-08-31	1985-04-04	Epoxy-urethane avec liaison alcanolamine

Country Status (2)

Country	Link
US (1)	US4520185A (fr)
CA (1)	CA1230697A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4705841A (en) *	1986-03-21	1987-11-10	Sternson Limited	TBEA linked epoxy-urethanes
US6369188B1 (en)	1998-03-27	2002-04-09	Polymeright, Inc.	Polyfunctional urethane- or urea-containing oligomers and polymers prepared therefrom
US7615604B2 (en) *	2003-01-17	2009-11-10	The United States Of America As Represented By The Secretary Of The Navy	Diols formed by ring-opening of epoxies
US7622541B2 (en) *	2003-01-17	2009-11-24	The United States Of America As Represented By The Secretary Of The Navy	Polyurethane coating
EP2931781B1 (fr) *	2012-12-14	2020-11-04	Blue Cube IP LLC	Résines époxyde modifiées
CN103524703B (zh) *	2013-10-09	2015-06-10	山西凌云聚氨酯有限公司	一种聚氨酯/环氧树脂复合材料的制备方法
WO2018081032A1 (fr) *	2016-10-25	2018-05-03	Dow Global Technologies Llc	Adhésif époxyde présentant une résistance aux chocs à basse température améliorée

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA672467A (en) *		1963-10-15	Windemuth Erwin	Polyurethane plastics
US2830038A (en) *	1957-05-07	1958-04-08	Du Pont	Poly (polyalkylene ether urethane) polymers containing terminal epoxide groups
US3020262A (en) *	1957-12-19	1962-02-06	Jefferson Chem Co Inc	Method for producing 2-oxazolidones from epoxides and isocyanates
US3445436A (en) *	1966-06-14	1969-05-20	Tremco Mfg Co	Polyurethane polyepoxides
DE1720492B1 (de) *	1966-08-04	1972-05-31	Dow Chemical Co	Verfahren zur herstellung von modifizierten epoxypolyaddukten
US3763079A (en) *	1971-06-01	1973-10-02	Du Pont	Polyurethanes based on mixed aromatic aliphatic polyesters
US3931116A (en) *	1972-08-14	1976-01-06	Witco Chemical Corporation	Curable amine-terminated polyurethane-urea-epoxide lacquers
US4111917A (en) *	1976-05-11	1978-09-05	W. R. Grace & Co.	Use of latent amines to cure epoxy resins
US4143009A (en) *	1977-03-02	1979-03-06	Frank Dewey	Polyurethane-epoxy casting resin
US4267288A (en) *	1978-04-24	1981-05-12	E. I. Du Pont De Nemours And Company	Epoxy-urethanes based on copolyesters
US4282123A (en) *	1979-08-06	1981-08-04	Mobil Oil Corporation	Elastomeric urethane coating

1984
- 1984-08-31 US US06/646,702 patent/US4520185A/en not_active Expired - Fee Related
1985
- 1985-04-04 CA CA000478524A patent/CA1230697A/fr not_active Expired

Also Published As

Publication number	Publication date
US4520185A (en)	1985-05-28

Legal Events

Date	Code	Title	Description
2005-04-04	MKEX	Expiry

Publication	Publication Date	Title
US4578424A (en)	1986-03-25	High performance two-component epoxy structural adhesives with chemical thixotropy
US4668736A (en)	1987-05-26	Fast curing epoxy resin compositions
US7300963B2 (en)	2007-11-27	Hardeners for water-based epoxy resin systems and processes for using the same
US4728384A (en)	1988-03-01	Two component epoxy structural adhesives with improved flexibility
EP0171198B1 (fr)	1989-02-22	Compositions liquides durcissables de polymères terminés par des groupes d'époxy et de mercaptan
US4143009A (en)	1979-03-06	Polyurethane-epoxy casting resin
US5219975A (en)	1993-06-15	Process for the preparation of amines, the amines thus obtained and the use thereof as hardeners for epoxide resins
US5480958A (en)	1996-01-02	Polyepoxide resins incorporating epoxy terminated urethanes as tougheners
US4683282A (en)	1987-07-28	Novel boron trifluoride-poly (alkylene oxide) amine catalysts for curing epoxy resins
US4740539A (en)	1988-04-26	Flexible two-component epoxy structural adhesives
CA1230697A (fr)	1987-12-22	Epoxy-urethane avec liaison alcanolamine
JP7385675B2 (ja)	2023-11-22	変性エポキシ樹脂に基づく２成分（２ｋ）組成物
US4870150A (en)	1989-09-26	Polyurethanes made from blends of polypropyleneoxide polyol and polybutyleneoxide polyol intermediates
US4804710A (en)	1989-02-14	Epoxy resin composition
US4705841A (en)	1987-11-10	TBEA linked epoxy-urethanes
US4418166A (en)	1983-11-29	High temperature resistant adhesive bonding composition of epoxy resin and two-part hardener
US3838110A (en)	1974-09-24	Inherently mold-releasable mold or casting composition
US4728737A (en)	1988-03-01	High performance two-component epoxy structural adhesive with chemical thixotropy
US6465598B2 (en)	2002-10-15	Urethane resins
US5153296A (en)	1992-10-06	Epoxide resin mixtures which harden at room temperature
US3886228A (en)	1975-05-27	Polyurethane composition curable with polyamine/acid anhydride adduct
EP1204691A1 (fr)	2002-05-15	Systemes reactifs exempts de solvants et durcissant a temperature ambiante et leur utilisation pour la production d'adhesifs, de masses d'etancheite, de masses de remplissage, de pieces moulees ou de revetements
EP0246875A2 (fr)	1987-11-25	Polymères liquides
US6878794B1 (en)	2005-04-12	Urethane resins
KR920009737B1 (ko)	1992-10-22	에폭시 수지 조성물